Ammonia → 3-Amino-3[2-(4-ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-phenylacetamido]-4-methylazetidin-2-one

HRID 1905659Notes

Reaction equation

HRID 1905659 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]([NH:11][CH:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:13]([NH:15][C:16]2(S(C)=O)[CH:19]([CH3:20])[NH:18][C:17]2=[O:21])=[O:14])=[O:10])[C:5](=[O:31])[C:4]1=[O:32])[CH3:2].[NH3:33]>O1CCOCC1>[NH2:33][C:16]1([NH:15][C:13](=[O:14])[CH:12]([NH:11][C:9]([N:6]2[CH2:7][CH2:8][N:3]([CH2:1][CH3:2])[C:4](=[O:32])[C:5]2=[O:31])=[O:10])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]([CH3:20])[NH:18][C:17]1=[O:21]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 201628533[2-(4-Ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-phenylacetamido]-4-methyl-3-methylsulphinylazetidin-2-one

Product 1

HCID 201628613-Amino-3[2-(4-ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-phenylacetamido]-4-methylazetidin-2-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The sulphoxide (61) (145 mg) in dioxan (5 ml) was treated with ammonia (21 ml) overnight at room temperature. The solvent was then evaporated and the residue chromatographed on silica gel to give the product (62) as a white solid (95 mg), νmax. (CHCl3) 3400, 3280, 1770, 1715 and 1690 cm-1, δ (CDCl3) 0.87, 0.90, 1.10 and 1.14 (each d, J 6 Hz, together 3H), 1.20 (t, J 7 Hz, 3H), 1.6-2.9 br (2H, exch.), 3.40-3.65 (m, 4H) (irradiation at 0.90 caused this signal to simplify), 3.85 (2xq, J 7 Hz, together 1H) (irradiation at 0.87 or 1.10 caused one of the above signals to collapse to a s), 3.95-4.13(m, 2H), 5.45(2xd, J 7 Hz, together 1H, collapses to 2 xs on exch), 6.50, 6.58, 6.63, and 6.72 br (each s, together 1H, exch.), 7.25-7.56 (m, 5H), 7.62, 7.76, 7.90, and 8.06 br (each s, 1H, exch.), and 9.90 (2xd, J 7 Hz, together 1H, exch.).

Workup

  1. customThe solvent was then evaporated
  2. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-14988a8842a1433199a46f750b4908d9
Source dataset
uspto-grants-1987_03
Patent number
US04647558

Reaction notes

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